Dodecanedien-1-ol and dodecen-1-ol or their mixtures as aroma chemicals

Abstract

The present invention relates to dodecanedien-1-ol, dodecen-1-ol or mixtures thereof and processes for their preparation, the use of dodecanedien-1-ol, dodecen-1-ol or mixtures thereof as aroma chemicals; the use of dodecanedien-1-ol, dodecen-1-ol or mixtures thereof for preparing aroma chemical compositions or modifying the aroma character of aroma chemical compositions; aroma chemical compositions comprising dodecanedien-1-ol, dodecen-1-ol or mixtures thereof; and processes for preparing perfumed compositions or modifying the aroma character of perfumed compositions.

Description

[Technical Field]

[0001] The present invention relates to dodecanedien-1-ol and dodecen-1-ol or mixtures thereof and processes for their preparation, the use of dodecanedien-1-ol and dodecen-1-ol or mixtures thereof as aroma chemicals; the use of dodecanedien-1-ol and dodecen-1-ol or mixtures thereof for preparing aroma chemical compositions or modifying the aroma character of aroma chemical compositions; aroma chemical compositions comprising dodecanedien-1-ol and dodecen-1-ol or mixtures thereof; and processes for preparing perfumed compositions or modifying the aroma character of perfumed compositions. [Background technology]

[0002] Aroma chemicals, and in particular fragrances, are of great interest, especially in the fields of cosmetics and cleaning and laundry compositions. Naturally derived fragrances are often expensive, their availability is often limited, and their content, purity, etc. may vary with changing environmental conditions. Therefore, to avoid these undesirable factors, there is great interest in creating synthetic materials that have organoleptic properties similar to those of more expensive natural fragrances, or that have novel and interesting organoleptic profiles.

[0003] Despite the large number of aroma chemicals (fragrances and flavorings) already in existence, new ingredients are constantly needed to be able to meet the numerous properties desired for a wide variety of fields of application. These primarily include organoleptic properties, i.e., the compounds should have advantageous odor (olfactory) or taste properties. Furthermore, aroma chemicals should also have additional favorable secondary properties, such as efficient preparation methods, the possibility of providing a better sensory profile as a result of synergistic effects with other fragrances, greater stability under specific application conditions, greater scalability, better and longer lasting properties, etc.

[0004] There is an increasing need for fragrance chemicals that can impart a fragrance impression to a composition, especially a woody / fruity / sweet / dried fruit / floral / orris / powdery / food-like fragrance impression. Such properties are particularly interesting for compositions such as body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, and fragrance dispenser compositions. Of particular interest are fragrance chemicals that can impart one or more distinct fragrance impressions to a composition, thereby contributing to the composition's rich and interesting sensory profile, especially its olfactory profile. Furthermore, particularly for fragrance chemicals that can impart a fragrance impression, substantivity and tenacity are of particular interest in order to obtain a long-lasting fragrance impression in the composition and on surfaces treated with the composition.

[0005] However, the search for a substance with a specific sensory property (e.g., a specific odor) is extremely difficult because even small changes in chemical structure can result in large changes in sensory properties such as odor and / or taste. Thus, the search for new fragrances and flavors is often difficult, time-consuming, and laborious, and it is unclear whether a substance with the desired odor and / or taste will actually be found. Summary of the Invention

[0006] The aim of the present invention is to provide new aroma chemicals, which should have pleasant organoleptic properties.

[0007] A further object of the present invention is to provide materials that can be used as aroma chemicals in ready-to-use compositions, and particularly strong-smelling materials with a pleasant odor are sought. Furthermore, they should be capable of being combined with other aroma chemicals to create new and advantageous sensory profiles. Furthermore, these aroma chemicals should be obtainable from readily available starting materials, allowing their rapid and economical production.

[0008] This object is achieved by providing novel compounds, such as dodecanedien-1-ol or dodecen-1-ol, or mixtures thereof. The inventors have found that these compounds and / or mixtures have a pleasant odor evoking an impression selected from the group consisting of an aldehydic note, a fatty note, a mandarin note, a clean linen note, a floral note, a marine note, a citrus note, a metallic note, a waxy note, and a green note.

[0009] Summary of the Invention Thus, a first aspect of the present invention relates to the use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol for imparting a fragrance impression to a composition.

[0010] In particular, the use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol for imparting a fragrance impression to a composition.

[0011] A second aspect of the present invention relates to a method for imparting a fragrance impression to a composition, the method comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecane-1-ol.

[0012] In particular, a method for imparting a fragrance impression to a composition, said method comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol.

[0013] A third aspect of the present invention is a) at least one compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol; and b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol; and c) Dodecan-1-ol The present invention relates to a mixture comprising:

[0014] A fourth aspect of the present invention relates to an aroma chemical composition comprising a compound / mixture of the present invention and (i) at least one additional aroma chemical different from the compound of the present invention, or (ii) at least one non-aroma chemical carrier, or (iii) a mixture of (i) and (ii).

[0015] A fifth aspect of the present invention relates to the use of the compounds / mixtures of the present invention for preparing aroma chemical compositions.

[0016] A sixth aspect of the present invention relates to the use of the compounds / mixtures of the present invention to modify the aroma characteristics of aroma chemical compositions.

[0017] A seventh aspect of the present invention relates to methods of preparing the compounds of the present invention.

[0018] An eighth aspect of the present invention relates to a method of preparing an aroma chemical composition, said method comprising the step of mixing a compound of the present invention with other ingredients, such as at least one other aroma chemical and / or at least one non-aroma chemical carrier, to obtain an aroma chemical composition.

[0019] A ninth aspect of the present invention relates to a method for modifying the aroma of an aroma chemical composition, said method comprising the step of incorporating a compound of the present invention into the aroma chemical composition to obtain an aroma-modified aroma chemical composition.

[0020] A tenth aspect of the present invention relates to a method for modifying the aroma of a ready-to-use composition, said method comprising the step of incorporating a compound of the present invention into the ready-to-use composition to obtain a ready-to-use composition with modified aroma.

[0021] The compounds of the present invention and their aroma chemical compositions have advantageous organoleptic properties, in particular a pleasant fragrance, and can therefore be preferably used as perfuming ingredients in perfume compositions, body care compositions (including cosmetic compositions and oral and dental hygiene products), hygiene products, cleaning compositions (including dishwashing compositions), fabric detergent compositions, fragrance dispenser compositions, foods, dietary supplements, pharmaceutical compositions, crop protection compositions and other ready-to-use compositions.

[0022] The pleasant fragrance, low volatility, and excellent solubility of the compounds of the present invention make them suitable ingredients in compositions where a pleasant fragrance is desired. The physical properties of the compounds of the present invention allow them to be well combined with other fragrance chemicals and conventional ingredients in fragranced, ready-to-use compositions, e.g., particularly perfume compositions. This allows, for example, the creation of fragrance compositions, particularly perfume compositions, with novel and advantageous sensory profiles.

[0023] Furthermore, the compounds of the present invention can be prepared in excellent yield and purity by simple synthesis starting from readily available starting materials, and therefore can be produced on a large scale in a simple and cost-effective manner. DETAILED DESCRIPTION OF THE INVENTION

[0024] Detailed Description of the Invention The following detailed description is merely exemplary in nature and is not intended to limit the invention or the application and uses of the invention. Furthermore, there is no intention to be bound by any theory presented in the preceding technical field, background, brief summary or the following detailed description.

[0025] As used herein, the terms "comprising," "comprises," and "comprised of" are synonymous with "including," "includes," or "containing," and "contains," and are inclusive or open-ended and do not exclude additional, unrecited elements, components, or method steps. As used herein, the terms "comprising," "comprises," and "comprised of" will be understood to include the terms "consisting of," "consists," and "consists of."

[0026] Furthermore, terms such as "(a)," "(b)," "(c)," "(d)," etc. in the specification and claims are used to distinguish between similar elements and are not necessarily intended to describe a sequential or chronological order. It is to be understood that terms so used are interchangeable under appropriate circumstances, and that embodiments of the subject matter described herein are capable of operation in orders other than those described or illustrated herein. When terms such as "(A)," "(B)," and "(C)" or AA), BB), and CC) or "(a)," "(b)," "(c)," "(d)," "(i)," "(ii)," etc. refer to steps of a method or use or assay, unless otherwise indicated in the application set forth herein above or below, there is no time or time interval coherence between the steps, i.e., steps may be performed simultaneously, or there may be time intervals of seconds, minutes, hours, days, weeks, months, or even years between such steps.

[0027] In the following passages, various aspects of the present subject matter are defined in more detail. Each aspect so defined may be combined with any other aspect(s), unless expressly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature(s) indicated as being preferred or advantageous.

[0028] References throughout this specification to "one embodiment," "an embodiment," or "a preferred embodiment" mean that a particular feature, structure, or characteristic described in connection with that embodiment is included in at least one embodiment of the present invention. Thus, appearances of the phrases "in one embodiment," "In a preferred embodiment," or "in a preferred embodiment" in various places throughout this specification do not necessarily all refer to the same embodiment, but may. Furthermore, in one or more embodiments, features, structures, or characteristics may be combined in any suitable manner, as would be apparent to one of ordinary skill in the art from this disclosure. Furthermore, some embodiments described herein include some features but not other features included in other embodiments, and combinations of features from different embodiments are meant to form different embodiments within the scope of the present subject matter, as would be understood by one of ordinary skill in the art. For example, in the appended claims, any of the claimed embodiments may be used in any combination.

[0029] Furthermore, ranges defined throughout this specification are inclusive of the end values, i.e., a range of 1 to 10 means that both 1 and 10 are included within the range. For the avoidance of doubt, applicants reserve the right to any and all equivalents pursuant to applicable law.

[0030] definition In the context of the present invention, the term "aroma" refers to sensory properties and includes smell and / or flavor.

[0031] The term "aromachemical" refers to a substance used to obtain a sensory or organoleptic impression (used interchangeably herein), including its use to obtain an olfactory and / or flavor impression. The term "olfactory impression" refers to an odor impression that is not accompanied by either a positive or negative judgment, whereas the terms "scent impression" or "fragrance impression" or "aroma impression" (used interchangeably herein) as used herein are associated with an odor impression that is generally perceived as pleasant. Thus, "fragrance" or "aroma" refers to an aromachemical that primarily induces a pleasant odor impression. Flavor induces a taste impression.

[0032] As used herein, the term "fragrance composition" refers to a composition that induces a fragrance. The term fragrance composition includes "odor composition" and / or "flavor composition." An odor composition is a composition that primarily induces an odor impression, and a flavor composition is a composition that primarily induces a taste impression.

[0033] The term "olfactory composition" includes "fragrance compositions" or "scent compositions" (used interchangeably herein) that induce primarily an olfactory impression that is generally perceived as pleasant.

[0034] The common hedonic expressions "advantageous sensory properties" or "advantageous organoleptic properties" describe the pleasantness and conciseness of the sensory impression conveyed by aroma chemicals. "Pleasantness" and "simplicity" are terms well known to those skilled in the art, such as perfumers. "Pleasantness" generally refers to a naturally occurring, well-perceived, pleasant sensory impression. However, "nice" need not be synonymous with "sweet." "Pleasant" can also be the smell of musk or sandalwood. "Simplicity" generally refers to a naturally occurring sensory impression that is reproducibly and identically reminiscent of something specific to the same test panel. For example, a substance may have an odor that is naturally reminiscent of the odor of "apple," and this odor will then simply be an "apple" odor. If the apple smell were very pleasant, for example, because it reminded one of a sweet, ripe apple, the smell would be called "pleasant." However, the smell of a typically sour apple may also be plain. If both reactions occur upon smelling the substance, thus in this example giving rise to a pleasant, plain apple smell, then the substance has particularly advantageous sensory properties.

[0035] The phrases "combination of," "in combination with," or "combining with," as used herein, refer to a composition, method, or use of two compounds, taking into account the fact that the two compounds need not be used in the form of a physical mixture of said compounds, but can be used (e.g., added) separately. When compounds are used separately, they can be used (e.g., added) sequentially in any order (i.e., one after the other) or simultaneously (i.e., essentially simultaneously).

[0036] The term "boosting" or "boost" is used herein to describe the effect of enhancing and / or modifying the aroma of a fragrance chemical or composition. The term "enhancing" includes increasing the pleasantness and / or simplicity of the fragrance and / or increasing the intensity. The term "modifying" includes changing the aroma profile.

[0037] The intensity can be determined by threshold measurements: the odor threshold is the concentration of a substance in the relevant gas space at which an odor impression can still only be perceived by a representative test panel, but this no longer needs to be defined.

[0038] A booster effect is particularly desirable in fragrance compositions when the application calls for a top note characterized by a particularly rapid and intense odor delivery, for example in air fresheners in deodorants or chewing gum in the taste category.

[0039] The terms "the present invention relates to" and "the present invention is directed to" are used interchangeably throughout the present invention.

[0040] The terms "compound" and "substance" are used interchangeably throughout this invention.

[0041] The term "tenacity" describes the evaporation behavior of a fragrance chemical over time. Tenacity can be determined, for example, by applying the fragrance chemical to a test strip and then olfactory evaluation of the odor impression of the test strip. For fragrance chemicals with high tenacity, the panel can still discern the fragrance impression for a long period of time.

[0042] The term "substantivity" describes the interaction of fragrance chemicals with a surface, such as skin or a fabric, particularly after subsequent treatment of the surface (e.g., washing). Substantivity can be determined, for example, by washing fabrics with a fabric detergent composition comprising the fragrance chemicals and then by olfactory evaluation of the fabrics immediately after washing (wet fabrics) as well as evaluation of the dried fabrics after extended storage.

[0043] The term "stability" describes the behavior of a fragrance chemical when in contact with oxygen, light, and / or other substances. A fragrance chemical with high stability maintains its fragrance profile over time, preferably in various compositions, and under various storage conditions.

[0044] Preferably, the staying power, persistence and stability of the fragrance chemicals in the composition should be high in order to impart a long-lasting fragrance impression to the composition or to surfaces treated with the composition.

[0045] Unless otherwise specified herein, the "compound" and non-stereospecific compound names, such as "4,8-dodecadien-1-ol," described herein are not intended to be limited to any stereoisomer or mixture of specific stereoisomers. Thus, the compound of the present invention may be a single stereoisomer of 4,8-dodecadien-1-ol selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, and (4Z,8Z)-dodeca-4,8-dien-1-ol, or may be a mixture of two or more of these stereoisomers of 4,8-dodecadien-1-ol.

[0046] compound : One embodiment of the present invention is directed to a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol, and dodecan-1-ol.

[0047] In a preferred embodiment, the compound is selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol.

[0048] In another embodiment of the present invention, the compound of the present invention is (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca The compound may be a single stereoisomer selected from the group consisting of (4E)-dodeca-4,11-dien-1-ol, (4Z)-dodeca-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecane-1-ol.

[0049] Preferably, the compound of the present invention may be a single stereoisomer selected from the group consisting of 4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol, and (4Z)dodeca-4,11-dien-1-ol.

[0050] mixture In yet another embodiment, the present invention provides: a) at least one compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol; and b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol The present invention relates to a mixture containing:

[0051] In yet another embodiment of the present invention, the dodeca-4,8-dien-1-ol is selected from the group consisting of (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol.

[0052] In yet another embodiment of the present invention, the dodeca-8,11-dien-1-ol is selected from the group consisting of (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

[0053] In yet another embodiment of the present invention, the dodeca-4,11-dien-1-ol is selected from the group consisting of (4E) dodeca-4,11-dien-1-ol and (4Z) dodeca-4,11-dien-1-ol.

[0054] In yet another embodiment of the present invention, the 4-dodecen-1-ol is selected from the group consisting of (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

[0055] In a further embodiment of the present invention, the 8-dodecen-1-ol is selected from the group consisting of (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

[0056] In an embodiment of the present invention, the mixture further comprises dodecan-1-ol.

[0057] use : One embodiment of the present invention is directed to the use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol to impart a fragrance impression to a composition.

[0058] Preferably, the present invention is directed to the use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol for imparting a fragrance impression to a composition.

[0059] In an embodiment of the present invention, a compound selected from the group consisting of (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecan-1-ol is useful as a fragrance chemical.

[0060] Preferably, compounds selected from the group consisting of (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol are useful as aroma chemicals.

[0061] In an embodiment of the present invention, the compounds / mixtures of the present invention or aroma chemical compositions comprising said compounds / mixtures are used as fragrances.

[0062] In particular, the compounds of the present invention are used to impart notes reminiscent of aldehyde notes, fatty notes, mandarin notes, clean linen notes, floral notes, marine notes, citrus notes, metallic notes, waxy notes, violet leaf notes and green notes.

[0063] The compounds / mixtures of the present invention can generally be used in ready-to-use compositions, particularly in fragranced ready-to-use compositions.As used herein, "fragranced ready-to-use compositions" refer to ready-to-use compositions that primarily induce a pleasant odor and / or taste impression.In a preferred embodiment, the fragranced ready-to-use compositions are perfumed ready-to-use compositions, i.e., induce a pleasant odor.

[0064] Perfumed ready-to-use compositions are, for example, compositions used in personal care, home care, in industrial applications, as well as compositions used in other applications, such as, for example, pharmaceutical compositions or crop protection compositions.

[0065] Preferably, the compounds of the present invention are used in a composition selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions and oral and dental hygiene products), hygiene products, cleaning compositions (including dishwashing compositions), fabric detergent compositions, scent dispenser compositions, food products, dietary supplements, pharmaceutical compositions and crop protection compositions, in which the compounds of the present invention are used as aroma chemicals, preferably as fragrances.

[0066] In particular, the compounds of the present invention are used to impart notes reminiscent of dried fruit, floral, sweet, orris or powdery elements to the compositions listed above; or to produce aromas reminiscent of sweet, floral or fruity elements.

[0067] Details of the above listed compositions are provided below.

[0068] Similarly, the compounds of the present invention may improve the sensory profile of an aroma chemical composition as a result of a synergistic effect with other aroma chemicals (e.g., other fragrances) contained in the composition, which means that the compounds may provide a booster effect for said other aroma chemicals, and are therefore suitable as boosters of other aroma chemicals.

[0069] Accordingly, the present invention also relates to the use of the compounds of the present invention to modify the aroma characteristics (e.g., scent characteristics) of perfumed (e.g., fragranced) compositions; and in particular, to their use as boosters of other aroma chemicals.

[0070] The booster effect of a substance means that the substance enhances and intensifies the overall sensory (e.g., olfactory) impression of an aromachemical preparation (e.g., perfume preparation, etc.). For example, in the mint range, although the pure substance menthyl methyl ether itself does not produce any particular strong odor, it is known to enhance the flavor or taste mixture of peppermint oil, resulting in a significantly stronger and more complex perception, especially in the top note. In fragrance applications, Hedione® (methyl dihydrojasmonate) only exhibits a light floral jasmine note as a pure substance, but as an odor booster, it enhances the diffusion, freshness, and volume of perfume compositions. The booster effect is particularly desirable when applications require a top note characterized by a particularly rapid and strong odor impression, such as in air fresheners in deodorants or chewing gum in the taste category.

[0071] To achieve such a booster effect, the compounds of the present invention may be used, for example, in an amount of 0.001 to 10% by weight (wt. %), for example 0.01 to 2 wt. %, preferably 0.05 to 1 wt. %, especially 0.1 to 0.5 wt. %, based on the total weight of the resulting aromachemical composition.

[0072] Additionally, the compounds of the present invention may have additional beneficial effects on the compositions they are used in. For example, the compounds may enhance the overall performance of the compositions in which they are incorporated, such as the stability (e.g., formulation stability), extendibility, or durability of the composition.

[0073] method : Dodecanedien-1-ol and dodecen-1-ol or mixtures thereof can be prepared by standard methods of organic chemistry and methods described in the art. More precisely, dodecanedien-1-ol and dodecen-1-ol or mixtures thereof can be prepared by subjecting 4,8,11-dodecatrienal to hydrogenation to form dodecanedien-1-ol and dodecen-1-ol or mixtures thereof. In particular, 4-dodecadien-1-ol and 8-dodecadien-1-ol as a mixture of cis / trans isomers and 4,8-dodecadien-1-ol are obtained.

[0074] The above reaction can be carried out, for example, analogously to the method described by Liebigs Annalen der Chemie (1982), (8), 1478-94.

[0075] In some embodiments, depending on the hydrogenation time, different ratios of the corresponding alcohols can be obtained as determined by H-NMR (olefins vs. methylene).

[0076] In certain embodiments, the catalyst used for the reaction is selected from the group consisting of ruthenium, iridium, rhodium, platinum, and palladium.

[0077] In one embodiment, the reaction was carried out at a temperature in the range of 50°C to 70°C, preferably 50°C to 65°C, and more preferably 50°C to 60°C.

[0078] In one embodiment, the reaction is carried out at a pressure in the range of 25 bar to 40 bar, preferably 25 bar to 35 bar, more preferably 25 bar to 30 bar.

[0079] In some embodiments, the reaction is carried out for 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 13 hours, 14 hours, 15 hours, '6 hours, '7 hours, 18 hours, 19 hours, 20 hours.

[0080] In one embodiment of the invention, tertiary amines are used as catalysts / activators in the above reaction. Tri-n-alkylamines, especially triethylamine, tri-n-propylamine, tri-n-butylamine and trimethylamine are preferred.

[0081] In one embodiment, 4,8,11-dodecatrienal (1.2 kg, 82 mmol) was dissolved in methanol (800 g) in the presence of trimethylamine (48 g, 3 wt%) and a Ru / Fe catalyst (20 g, 1.6 wt%) in a 3.5 L autoclave. The hydrogenation reaction was carried out at T = 55 °C and 30 bar hydrogen pressure to give 4-dodecadien-1-ol and 8-dodecadien-1-ol as a mixture of cis / trans isomers, as well as 4,8-dodecadien-1-ol.

[0082] In one embodiment, the reaction time was 6 hours, and the percentages of dodecenol and dodecadienol obtained were 12% and 88%, respectively.

[0083] In yet another embodiment, the reaction time was 8 hours and the percentages of dodecenol and dodecadienol obtained were 40% and 60%, respectively.

[0084] In a further embodiment, the reaction time was 14 hours and the percentages of dodecenol and dodecadienol obtained were 66% and 34%, respectively.

[0085] composition : In one embodiment, the present invention provides a compound / mixture of the present invention, and: (i) at least one additional fragrance chemical; or (ii) at least one non-fragrance chemical carrier; or (iii) Both (i) and (ii) The present invention relates to a fragrance chemical composition comprising:

[0086] As used herein, the term "fragrance chemical composition" refers to a composition that induces the impression of a pleasant fragrance, e.g., a pleasant odor.

[0087] The non-fragrance chemical carriers in the fragrance chemical compositions of the present invention may be selected from surfactants, oil components and solvents, among others.

[0088] The additional fragrance chemicals are different from the compounds / mixtures of the present invention.

[0089] The physical properties of the compounds / mixtures described above allow them to be well combined with other aroma chemicals (e.g., other fragrances) and other conventional ingredients in perfumed (e.g., fragranced) ready-to-use compositions, such as, in particular, perfume compositions. This allows, for example, the creation of aroma compositions (e.g., perfume compositions) with novel and advantageous sensory profiles. In particular, as already explained above, the compounds can provide a booster effect for other aroma chemicals (e.g., other fragrances).

[0090] Thus, in one preferred embodiment, the aroma chemical composition comprises a compound of the present invention as defined herein; and at least one additional aroma chemical different from the compound / mixture of the present invention.

[0091] The additional fragrance chemical may be, for example, one, preferably two, three, four, five, six, seven, eight or more fragrance chemicals selected from the group consisting of: Geranyl acetate, alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyl linalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and / or 4,7-methano-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol, citronellyl acetate, tetrahydrogeraniol, vanillin, linalyl acetate, styryl acetate, octahydro-2,3,8,8-tetramethyl-2-acetonaphthone and / or 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl a Acetate, alpha-ionone, n-alpha-methylionone, alpha-isomethylionone, coumarin, terpinyl acetate, 2-phenylethyl alcohol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, alpha-amylcinnamaldehyde, ethylene brassylate, (E)- and / or (Z)-3-methylcyclopentadeca-5-enone, 15-pentadec-11-enolide and / or 15-pentadec-12-enolide, 15-cyclopentadecanolide, 1-(5,6,7 ,8-Tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)ethanone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenecarboxaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6-Dimethyl-5-hepten-1-al, borneol, 3-(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-one octahydronaphthalen-2-ol, 3-(4-tert-butylphenyl)-propanal, ethyl 2-methylpentanoate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2-tert-butylcyclohexyl)acetate, and 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexan-1-ol.

[0092] In yet another preferred embodiment, the at least one fragrance chemical (i) is selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and methyl benzoate.

[0093] In yet another preferred embodiment, the at least one aroma chemical (i) is selected from the group consisting of ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0094] Further fragrance chemicals which may be combined with the compounds of the invention to produce compositions according to the invention can be found, for example, in the self-published books by S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001. In particular, the following may be mentioned:

[0095] Extracts derived from natural sources, such as essential oils, concrete, absolutes, resins, resinoids, balsams, tinctures, e.g.

[0096] Ambergris Tincture, Amyris Oil, Angelica Seed Oil, Angelica Root Oil, Anise Oil, Valerian Oil, Basil Oil, Tree Moss Absolute, Bay Oil, Artemisia Oil, Benzoin Resin, Bergamot Oil, Beeswax Absolute, Birch Tar Oil, Bitter Almond Oil, Safflower Oil, Boucle Leaf Oil, Cabreuva Oil, Cade Oil, Calamus Oil, Camphor Oil, Cananga Oil, Cardamom Oil, Cascarilla Oil, Cassia Oil, Cassia Absolute, Castoreum Absolute, Cedar Leaf Oil, Cedarwood Oil, Cistus Oil, Citronella Oil, Lemon Oil, Copaiba Balsam, Copaiba Balsam Oil, Coriander Oil, Costus Root Oil, Cumin Oil, Cypress Oil, Davana Oil, Dill Weed Oil, Dill Seed Oil, Eau de brouts absolute absolute), oakmoss absolute, elemi oil, tarragon oil, eucalyptus citriodora oil, eucalyptus oil, fennel oil, pine needle oil, galbanum oil, galbanum resin, geranium oil, grapefruit oil, guaiac wood oil, gharjan balsam, gharjan balsam oil, helichrysum absolute, helichrysum oil, ginger oil, iris root absolute, iris root oil, jasmine absolute, calamus oil, blue chamomile oil, Roman chamomile oil, carrot seed oil, cascarilla oil, pine needle oil, spearmint oil, caraway oil, labdanum oil, labdanum absolute, labdanum resin, lavandin absolute, lavender absolute, lavender oil, lemongrass oil, lovage oil, distilled lime oil, pressed lime oil, linalool oil, litseacubeba oil, laurel leaf oil, mace oil, marjoram oil, mandarin oil, massoia bark oil, mimosa absolute, musk seed oil, musk tincture, clary sage oil, nutmeg oil, myrrh absolute, myrrh oil, myrtle oil, clove leaf oil, clove flower oil, neroli oil, frankincense absolute, frankincense oil, opopanax oil, orange flower absolute, orange oil, origanum oil, palmarosa oil, patchouli oil, perilla oil, balsam of Peru oil, parsley leaf oil, parsley seed oil, petitgrain oil, pepper mint oil, pepper oil, pimento oil, pine oil, pennyroyal oil, rose absolute, rosewood oil, rose oil, rosemary oil, Dalmatian sage oil, Spanish sage oil, sandalwood oil, celery seed oil, spike lavender oil, star anise oil, styrax oil, tagetes oil, fir needle oil, tea tree oil, turpentine oil, thyme oil, tolu balsam, tonka absolute, tuberose absolute, vanilla extract, violet leaf absolute, verbena oil, vetiver oil, juniper berry oil, wine lees oil, wormwood oil, wintergreen oil, hyssop oil, civet absolute, cinnamon leaf oil, cinnamon bark oil and fractions thereof or components isolated therefrom,

[0097] individual fragrances selected from the group of hydrocarbons, such as 3-carene, alpha-pinene, beta-pinene, alpha-terpinene, gamma-terpinene, p-cymene, bisabolene, camphene, caryophyllene, cedrene, farnesene, limonene, longifolene, myrcene, ocimene, valencene, (E,Z)-1,3,5-undecatriene, styrene, diphenylmethane, etc.

[0098] aliphatic alcohols, such as hexanol, octanol, 3-octanol, 2,6-dimethylheptanol, 2-methyl-2-heptanol, 2-methyl-2-octanol, (E)-2-hexenol, (E)- and (Z)-3-hexenol, 1-octen-3-ol, a mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, 4-methyl-3-decen-5-ol, etc.

[0099] Aliphatic aldehydes and their acetals, such as hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tridecanal, 2-methyloctanal, 2-methylnonanal, (E)-2-hexenal, (Z)-4-heptenal, 2,6-dimethyl-5-heptenal, 10-undecenal, (E)-4-decenal, 2-dodecenal, 2,6,10-trimethyl-9-undecenal, and 2,6,10-trimethyl-5,9-undecadienal. methyl-3-heptanone, 5-methyl-3-heptanone oxime, 2,4,4,7-tetramethyl-6-octen-3-one, 6-methyl-5-hepten-2-one, etc.

[0100] Aliphatic sulfur-containing compounds, such as 3-methylthiohexanol, 3-methylthiohexyl acetate, 3-mercaptohexanol, 3-mercaptohexyl acetate, 3-mercaptohexyl butyrate, 3-acetylthiohexyl acetate, 1-menthene-8-thiol, etc.

[0101] Aliphatic nitriles, such as 2-nonenenitrile, 2-undecenenitrile, 2-tridecenenitrile, 3,12-tridecadienenitrile, 3,7-dimethyl-2,6-octadienenitrile, 3,7-dimethyl-6-octenenitrile, etc.

[0102] Esters of aliphatic carboxylic acids, for example, (E)- and (Z)-3-hexenyl formate, ethyl acetoacetate, isoamyl acetate, hexyl acetate, 3,5,5-trimethylhexyl acetate, 3-methyl-2-butenyl acetate, (E)-2-hexenyl acetate, (E)- and (Z)-3-hexenyl acetate, octyl acetate, 3-octyl acetate, 1-octen-3-yl acetate, ethyl butyrate, butyl butyrate, isoamyl butyrate, hexyl butyrate , (E)- and (Z)-3-hexenyl isobutyrate, hexyl crotonate, ethyl isovalerate, ethyl 2-methylpentanoate, ethyl hexanoate, allyl hexanoate, ethyl heptanoate, allyl heptanoate, ethyl octanoate, ethyl (E,Z)-2,4-decadienoate, methyl 2-octynate, methyl 2-nonynate, allyl 2-isoamyloxyacetate, methyl-3,7-dimethyl-2,6-octadienoate, 4-methyl-2-pentyl crotonate, etc.

[0103] Acyclic terpene alcohols, such as geraniol, nerol, linalool, lavandulol, nerolidol, farnesol, tetrahydrolinalool, 2,6-dimethyl-7-octen-2-ol, 2,6-dimethyloctan-2-ol, 2-methyl-6-methylene-7-octen-2-ol, 2,6-dimethyl-5,7-octadien-2-ol, 2,6-dimethyl-3,5-octadien-2-ol 3,7-dimethyl-4,6-octadien-3-ol, 3,7-dimethyl-1,5,7-octatrien-3-ol, 2,6-dimethyl-2,5,7-octatrien-1-ol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, and 3-methyl-2-butenoates,

[0104] Acyclic terpene aldehydes and ketones, such as geranial, neral, citronellal, 7-hydroxy-3,7-dimethyloctanal, 7-methoxy-3,7-dimethyloctanal, 2,6,10-trimethyl-9-undecenal, geranyl acetone, and the dimethyl- and diethyl acetals of geranial, neral, and 7-hydroxy-3,7-dimethyloctanal; cyclic terpene alcohols, such as menthol, isopulegol, alpha-terpi Neol, terpin-4-ol, menthan-8-ol, menthan-1-ol, menthan-7-ol, borneol, isoborneol, linalool oxide, nopol, cedrol, ambrinol, vetiverol, guajol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, and 3-methyl-2-butenoates, etc.

[0105] Cyclic terpene aldehydes and ketones, such as menthone, isomenthone, 8-mercaptomenthan-3-one, carvone, camphor, fenchone, alpha-ionone, beta-ionone, alpha-n-methylionone, beta-n-methylionone, alpha-isomethylionone, beta-isomethylionone, alpha-ionone, alpha-damascone, beta-damascone, beta-damascenone, delta-damascone, gamma-damascone, 1-(2,4,4-trimethyl-2- (cyclohexen-1-yl)-2-buten-1-one, 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-one, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, nootkatone, dihydronootkatone, 4,6,8-megastigmatrien-3-one, alpha-sinensal, beta-sinensal, acetylated cedarwood oil (methyl cedryl ketone), etc.

[0106] Cyclic alcohols, such as 4-tert-butylcyclohexanol, 3,3,5-trimethylcyclohexanol, 3-isocamphylcyclohexanol, 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, etc.

[0107] Alicyclic alcohols, for example, alpha-3,3-trimethylcyclohexylmethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol, 3-methyl- 5-(2,2,3-trimethyl-3-cyclopent-1-yl)pentan-2-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol, 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol, 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol, etc.

[0108] Cyclic and alicyclic ethers, such as cineole, cedryl methyl ether, cyclododecyl methyl ether, 1,1-dimethoxycyclododecane, (ethoxymethoxy)cyclododecane, alpha-cedrene epoxide, 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 3a-ethyl-6,6,9a-trimethyldodecahydro-naphtho[2,1-b]furan, 1,5,9-trimethyl-13-oxabicyclo-[10.1.0]trideca-4,8-diene, rose oxide, 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane, etc.

[0109] Cyclic and macrocyclic ketones, for example, 4-tert-butylcyclohexanone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-heptylcyclopentanone, 2-pentylcyclopentanone, 2-hydroxy-3-methyl-2-cyclopenten-1-one, 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one, 3-methyl-2-pentyl-2-cyclopenten-1-one, 3-methyl-4-cyclopentadecenone, 3-methyl-5-cyclopentadecenone, 3-methylcyclopentadecanone, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, 4-tert-pentylcyclohexanone, 5-cyclohexadecen-1-one, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 8-cyclohexadecen-1-one, 7-cyclohexadecen-1-one, (7 / 8)-cyclohexadecen-1-one, 9-cycloheptadecen-1-one, cyclopentadecanone, cyclohexadecanone, etc.

[0110] Alicyclic aldehydes, such as 2,4-dimethyl-3-cyclohexenecarbaldehyde, 2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, and 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde;

[0111] Alicyclic ketones, such as 1-(3,3-dimethylcyclohexyl)-4-penten-1-one, 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone, methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone, and tert-butyl(2,4-dimethyl-3-cyclohexen-1-yl)ketone;

[0112] Esters of cyclic alcohols, for example, 2-tert-butylcyclohexyl acetate, 4-tert-butylcyclohexyl acetate, 2-tert-pentylcyclohexyl acetate, 4-tert-pentylcyclohexyl acetate, 3,3,5-trimethylcyclohexyl acetate, decahydro-2-naphthyl acetate, 2-cyclopentylcyclopentylcrotonate, 3-pentyltetrahydro-2H-pyran-4-yl acetate , decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate, 4,7-methanooctahydro-5 or 6-indenyl acetate, etc.

[0113] Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate,

[0114] Esters of alicyclic carboxylic acids, for example, allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, cis- and trans-methyldihydrojasmonate, cis- and trans-methyljasmonate, methyl 2-hexyl-3-oxocyclopentanecarboxylate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate, ethyl 2-methyl-1,3-dioxolane-2-acetate, etc.

[0115] Aromatic aliphatic alcohols, such as benzyl alcohol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, 3-phenylpropanol, 2-phenylpropanol, 2-phenoxyethanol, 2,2-dimethyl-3-phenylpropanol, 2,2-dimethyl-3-(3-methylphenyl)propanol, 1,1-dimethyl-2-phenylethyl alcohol, 1,1-dimethyl-3-phenylpropanol, 1-ethyl-1-methyl-3-phenylpropanol, 2-methyl-5-phenylpentanol, 3-methyl-5-phenylpentanol, 3-phenyl-2-propen-1-ol, 4-methoxybenzyl alcohol, 1-(4-isopropylphenyl)ethanol, etc.

[0116] Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids, such as benzyl acetate, benzyl propionate, benzyl isobutyrate, benzyl isovalerate, 2-phenylethyl acetate, 2-phenylethyl propionate, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, 1-phenylethyl acetate, alpha-trichloromethylbenzyl acetate, alpha,alpha-dimethylphenylethyl acetate, alpha,alpha-dimethylphenylethyl butyrate, cinnamyl acetate, 2-phenoxyethyl isobutyrate, 4-methoxybenzyl acetate, etc.

[0117] Aromatic aliphatic ethers, such as 2-phenylethyl methyl ether, 2-phenylethyl isoamyl ether, 2-phenylethyl 1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydroatropaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxine, 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxine, etc.

[0118] Aromatic and araliphatic aldehydes, for example, benzaldehyde, phenylacetaldehyde, 3-phenylpropanal, hydroatropaldehyde, 4-methylbenzaldehyde, 4-methylphenylacetaldehyde, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 2-methyl-3-(4-isopropylphenyl)propanal, 2-methyl-3-(4-tert-butylphenyl)propanal, 2-methyl-3-(4-isobutylphenyl)propanal, 3-(4-tert-butylphenyl)propanal, cyclohexane, cinnamaldehyde, alpha-butylcinnamaldehyde, alpha-amylcinnamaldehyde, alpha-hexylcinnamaldehyde, 3-methyl-5-phenylpentanal, 4-methoxybenzaldehyde, 4-hydroxy-3-methoxy-benzaldehyde, 4-hydroxy-3-ethoxybenzaldehyde, 3,4-methylenedioxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 2-methyl-3-(4-methoxyphenyl)propanal, 2-methyl-3-(4-methylenedioxyphenyl)propanal, etc.

[0119] Aromatic and araliphatic ketones, for example, acetophenone, 4-methylacetophenone, 4-methoxyacetophenone, 4-tert-butyl-2,6-dimethylacetophenone, 4-phenyl-2-butanone, 4-(4-hydroxyphenyl)-2-butanone, 1-(2-naphthalenyl)-ethanone, 2-benzofuranylethanone, (3-methyl-2-benzofuranyl)ethanone, benzophenone, 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone, 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone, 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone, 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-acetonaphthone, etc.

[0120] Aromatic and aliphatic carboxylic acids and esters of aromatic and aliphatic carboxylic acids, for example, benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methyl phenyl acetate, ethyl phenyl acetate, geranyl phenyl acetate, phenylethyl phenyl acetate, methyl cinnamate, ethyl cinnamate, benzyl cinnamate, phenylethyl cinnamate, cinnamyl cinnamate, allyl phenoxyacetate, methyl salicylate, isoamyl salicylate, hexyl salicylate, cyclohexyl salicylate, cis-3-hexenyl salicylate, benzyl salicylate, phenylethyl salicylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl 3-phenylglycidate, ethyl 3-methyl-3-phenylglycidate, etc.

[0121] Nitrogen-containing aromatic compounds, such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene, 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone, cinnamonitrile, 3-methyl-5-phenyl-2-pentenonitrile, 3-methyl-5-phenylpentanonitrile, methyl anthranilate, methyl-N-methylanthranilate, Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde, 6-isopropylquinoline, 6-isobutylquinoline, 6-sec-butylquinoline, 2-(3-phenylpropyl)pyridine, indole, skatole, 2-methoxy-3-isopropyl-pyrazine, 2-isobutyl-3-methoxypyrazine, etc.

[0122] Phenols, phenyl ethers and phenyl esters, such as estragole, anethole, eugenol, eugenyl methyl ether, isoeugenol, isoeugenyl methyl ether, thymol, carvacrol, diphenyl ether, beta-naphthyl methyl ether, beta-naphthyl ethyl ether, beta-naphthyl isobutyl ether, 1,4-dimethoxybenzene, eugenyl acetate, 2-methoxy-4-methylphenol, 2-ethoxy-5-(1-propenyl)phenol, p-cresylphenyl acetate, etc.

[0123] Heterocyclic compounds, such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one, 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one, 3-hydroxy-2-methyl-4H-pyran-4-one, 2-ethyl-3-hydroxy-4H-pyran-4-one, etc.

[0124] Lactones, such as 1,4-octanolide, 3-methyl-1,4-octanolide, 1,4-nonanolide, 1,4-decanolide, 8-decen-1,4-olide, 1,4-undecanolide, 1,4-dodecanolide, 1,5-decanolide, 1,5-dodecanolide, 4-methyl-1,4-decanolide, 1,15-pentadecanolide, cis- and trans-11-pentadecan-1,15-olide, cis- and trans- s-12-pentadecen-1,15-olide, 1,16-hexadecanolide, 9-hexadecen-1,16-olide, 10-oxa-1,16-hexadecanolide, 11-oxa-1,16-hexadecanolide, 12-oxa-1,16-hexadecanolide, ethylene 1,12-dodecanedioate, ethylene 1,13-tridecanedioate, coumarin, 2,3-dihydrocoumarin, octahydrocoumarin, etc.

[0125] In a preferred embodiment, the at least one non-fragrance chemical carrier (ii) is selected from the group consisting of surfactants, oil components, antioxidants, deodorant actives and solvents.

[0126] In the context of the present invention, a "solvent" is one which does not itself have an aroma and serves to dilute the compound of the invention and / or any further components of the composition used according to the invention.

[0127] The amount of solvent(s) is selected depending on the composition.

[0128] In yet another preferred embodiment, the solvent is selected from the group consisting of ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, triethyl citrate, and isopropyl myristate.

[0129] In yet another preferred embodiment, the solvent is present in the composition in an amount of 0.01% to 99.0% by weight, more preferably 0.05% to 95.0% by weight, even more preferably 0.1% to 80.0% by weight, most preferably 0.1% to 70.0% by weight, and especially 0.1% to 60.0% by weight, relative to the total weight of the composition.

[0130] In yet another preferred embodiment of the present invention, the composition comprises from 0.05% to 10% by weight, more preferably from 0.1% to 5% by weight, and even more preferably from 0.2% to 3% by weight of solvent(s) relative to the total weight of the composition. In yet another preferred embodiment of the present invention, the composition comprises from 20% to 70% by weight, more preferably from 25% to 50% by weight of solvent(s) relative to the total weight of the composition.

[0131] One embodiment of the present invention is directed to a composition comprising a compound of the present invention and at least one oil component.

[0132] In preferred embodiments, the oil component is present in an amount of 0.1 to 80 wt. %, more preferably 0.5 to 70 wt. %, even more preferably 1 to 60 wt. %, even more preferably 1 to 50 wt. %, in particular 1 to 40 wt. %, more particularly 5 to 25 wt. %, and particularly 5 to 15 wt. %, relative to the total weight of the composition.

[0133] The oil component may be, for example, Guerbet alcohols based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, as well as other further esters, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate. , isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate, and erucyl erucate. 18 ~C 38 Alkylhydroxycarboxylic acids and straight or branched C6-C 22Esters with fatty alcohols (more particularly dioctyl malate), esters of linear and / or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimerdiol or trimertriol), C6-C 10 Triglycerides based on fatty acids, C6-C 18 Liquid mono-, di- and triglyceride mixtures based on fatty acids, C6-C 22 Esters of fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C 22 Fatty alcohol carbonates, such as Guerbet carbonates based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms, such as dicaprylyl carbonate (Cetiol® CC), benzoic acid and linear and / or branched C6-C 22 Also suitable are esters with alcohols (e.g. Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group, such as dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, and hydrocarbons, or mixtures thereof.

[0134] It should be understood that antioxidants can inhibit or prevent undesirable changes in the composition being protected caused by oxygen effects and other oxidative processes. The effect of antioxidants is, in most cases, that they act as free radical scavengers for the free radicals generated during autoxidation.

[0135] In a preferred embodiment, the antioxidant is selected from the group consisting of: amino acids (e.g., glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides, such as D,L-carnosine, D-carnosine, L-carnosine (= β-alanyl-L-histidine) and its derivatives, carotenoids, carotenes (e.g. alpha-carotene, beta-carotene, lycopene, lutein) or derivatives thereof, - chlorogenic acid and its derivatives, - lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl and glyceryl esters) and their salts, - Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts), sulfoximine compounds (e.g. buthionine sulfoximine, homocysteine ​​sulfoximine, buthionine sulfone, penta-, hexa-, heptathionine sulfoximine), - (metal) chelating agents (e.g., alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), - alpha hydroxy acids (e.g. citric acid, lactic acid, malic acid), - Humic acid, bile acids, bile extract, bilirubin, biliverdin, boldine (= alkaloid derived from the plant Peumus boldus), boldo extract, - EDTA, EGTA and their derivatives, - unsaturated fatty acids and their derivatives (e.g. gamma-linolenic acid, linoleic acid, oleic acid), - folic acid and its derivatives, - ubiquinone and ubiquinol and their derivatives, Vitamin C and derivatives (e.g., ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), - tocopherol and derivatives (e.g. vitamin E acetate), Vitamin A and derivatives (e.g. vitamin A palmitate), - Coniferyl benzoate of gum benzoin, rutic acid and its derivatives, alpha-glycosyl rutin, ferulic acid, furfurylidene glucitol, - Butylhydroxytoluene (BHT), Butylhydroxyanisole (BHA), - nordihydroguaiacic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, - superoxide dismutase, - zinc and its derivatives (e.g. ZnO, ZnSO4), - selenium and its derivatives (e.g. selenomethionine), and - stilbene and its derivatives (e.g. stilbene oxide, trans-stilbene oxide).

[0136] In a preferred embodiment, the antioxidant is selected from the group consisting of pentaerythrityl, tetra-di-t-butyl-hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate, and tocopherol.

[0137] In yet another preferred embodiment, the composition according to the present invention may contain an antioxidant in an amount of 0.001 to 25 wt %, preferably 0.005 to 10 wt %, more preferably 0.01 to 8 wt %, even more preferably 0.025 to 7 wt %, and even more preferably 0.05 to 5 wt %, relative to the total weight of the composition.

[0138] Deodorant compositions (deodorants and antiperspirants) suppress, mask, or eliminate body odor, which is formed through the action of skin bacteria during apocrine sweating, which leads to the formation of unpleasant-smelling degradation products.

[0139] Accordingly, one embodiment of the present invention is directed to a composition comprising a compound of the present invention and at least one deodorant active, hi a preferred embodiment, the deodorant active is selected from the group consisting of antiperspirants, esterase inhibitors, and antibacterial agents.

[0140] Suitable antiperspirants are selected from the group consisting of aluminum, zirconium, or zinc salts. Examples include aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, and their complex compounds (e.g., complex compounds with 1,2-propylene glycol), aluminum hydroxyallantoinate, aluminum chloride tartarate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, and their complex compounds (e.g., complex compounds with amino acids such as glycine). Aluminum chlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, and their complex compounds are preferably used.

[0141] In preferred embodiments, the antiperspirant is selected from the group consisting of aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate, aluminum hydroxy allantoinate, aluminum chloride tartrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, and aluminum zirconium pentachlorohydrate.

[0142] When sweat is present in the underarm area, extracellular enzymes, mainly proteases and / or lipases, are formed by bacteria, which decompose the esters present in sweat, releasing odors in the process.Suitable esterase inhibitors are, for example, trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, and especially triethyl citrate.Esterase inhibitors inhibit enzyme activity, thus suppressing odor formation.Free acid is likely released by cleavage of citrate esters, which lowers the pH value of skin to the extent that enzymes are inactivated by acylation. Other esterase inhibitors are sterol sulfates or phosphates, such as lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and their esters, such as citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, and zinc glycinate.

[0143] In preferred embodiments, the esterase inhibitor is selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid, malonic acid diethyl ester, citric acid, malic acid, tartaric acid, tartaric acid diethyl ester, and zinc glycinate.

[0144] The composition of the present invention contains the esterase inhibitor in an amount of 0.01 to 20% by weight, preferably 0.1 to 10% by weight, more particularly 0.5 to 5% by weight, based on the total weight of the composition.

[0145] As used herein, the term "antibacterial agent" encompasses substances that have bactericidal and / or bacteriostatic properties. Typically, these substances act against gram-positive bacteria and include, for example, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chloro ... ethanol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamides such as salicylic acid-n-octylamide or salicylic acid-n-decylamide.

[0146] In a preferred embodiment, the antimicrobial agent is chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1 4-chloro-3-(4-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerol monolaurate (GML), diglycerol monocaprate (DMC), salicylic acid-N-alkylamide.

[0147] The composition of the present invention contains the antibacterial agent in an amount of 0.01 to 5% by weight, preferably 0.1 to 2% by weight, based on the total weight of the composition.

[0148] In a preferred embodiment, the composition preferably comprises a surfactant.Due to the characteristic fragrance properties of the compounds of the present invention and their longevity, retention and stability, surfactants can be used in particular to provide an odor, preferably a fragrance impression or a fragrance impression, to surfactant-containing compositions, such as detergents (especially laundry care products and multi-purpose detergents).Preferably, surfactants can be used to impart a long-lasting flowery note and / or marine note and / or green note and / or sweet note and / or rubbery note and / or nutty note and / or woody note and / or dusty note and / or rooty note and / or lemon note odor impression to surfactant-containing compositions.

[0149] In a preferred embodiment, the surfactant is selected from the group consisting of anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, and zwitterionic surfactants, hi yet another preferred embodiment, the surfactant is an anionic surfactant.

[0150] Thus, the composition according to the present invention may preferably contain at least one surfactant. The surfactant(s) may be selected from anionic surfactants, nonionic surfactants, cationic surfactants, and / or amphoteric or zwitterionic surfactants. For example, surfactant-containing compositions such as shower gels, foam baths, shampoos, etc. preferably contain at least one anionic surfactant.

[0151] The compositions according to the present invention typically contain surfactant(s) in an aggregate amount of 0 to 40% by weight, preferably 0 to 20% by weight, more preferably 0.1 to 15% by weight, and especially 0.1 to 10% by weight, based on the total weight of the composition. Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alkyl(en)yl oligoglycosides or glucuronic acid derivatives, fatty acid N-alkylglucamides, protein hydrolysates (especially wheat-based plant products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates, and amine oxides. When the nonionic surfactant contains a polyglycol ether chain, it may have a conventional homolog distribution, but preferably has a narrow homolog distribution.

[0152] Zwitterionic surfactants contain at least one quaternary ammonium group and at least one COO group in the molecule. (-) or SO3 (-) These surfactants are surface-active compounds containing a hydroxyl group. Particularly suitable zwitterionic surfactants are so-called betaines, such as N-alkyl-N,N-dimethylammonium glycinates containing 8 to 18 carbon atoms in the alkyl or acyl group, such as cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, such as cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines, as well as cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. The fatty acid amide derivative of cocamidopropyl betaine, known by the CTFA name, is particularly preferred.

[0153] Amphoteric surfactants are particularly suitable as co-surfactants. Amphoteric surfactants include C8 to C 18 These surfactants are surface-active compounds that contain, in addition to an alkyl or acyl group, at least one free amino group and at least one -COOH or -SOH group in the molecule and are capable of forming inner salts. Examples of suitable amphoteric surfactants include N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids, and alkylaminoacetic acids, all of which contain approximately 8 to 18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionates, cocoacylaminoethylaminopropionates, and acylsarcosines.

[0154] Anionic surfactants are characterized by a water-soluble anionic group, such as a carboxylate group, a sulfate group, a sulfonate group, or a phosphate group, and a lipophilic group.A large number of dermatologically safe anionic surfactants are known to practitioners from relevant textbooks and are commercially available.Anionic surfactants are particularly alkyl sulfates, alkyl ether sulfates, alkyl ether carboxylates, acyl isethionates, acyl sarcosinates, linear C alkyl esters, in the form of alkali metal salts, ammonium salts, or alkanolammonium salts. 12 ~C 18 Acyl taurines containing alkyl or acyl groups, as well as sulfosuccinates and acyl glutamates in the form of alkali metal or ammonium salts.

[0155] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more particularly chlorides and bromides, such as alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, and trialkylmethylammonium chloride, such as cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride, and tricetylmethylammonium chloride. Furthermore, readily biodegradable quaternary ester compounds, such as dialkylammonium methosulfate and methylhydroxyalkyldialkoyloxyalkylammonium methosulfate, sold under the name Stepantexe, and the corresponding Dehyquart® series products, may also be used as cationic surfactants. "Esterquat" is generally understood to be a quaternized fatty acid triethanolamine ester salt. Esterquats can impart exceptional softness to the composition. Ester quats are known materials that are prepared by related organic chemistry methods. Other cationic surfactants suitable for use in accordance with the present invention are the quaternized protein hydrolysates.

[0156] One embodiment of the present invention is directed to a composition selected from the group consisting of a perfume composition, a body care composition, a hygiene product, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition, and a crop protection composition.

[0157] The composition is preferably an aroma chemical composition, more preferably a fragrance composition.

[0158] Suitable compositions are, for example, perfume compositions, body care compositions (including cosmetic compositions and oral and dental hygiene products), hygiene products, cleaning compositions (including dishwashing compositions), fabric detergent compositions, fragrance dispenser compositions, foods, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0159] The perfume composition may be selected from fine fragrances, air fresheners in liquid, gel or applied to a solid carrier, aerosol sprays, scented cleansers, scented candles and scented oils (e.g. lamp oils or massage oils).

[0160] Examples of fine fragrances are perfume extracts, eau de parfum, eau de toilette, eau de cologne, eau de solid, and extrait parfum.

[0161] Body care compositions include cosmetic compositions and oral and dental hygiene products, aftershave products, preshave products, splash colognes, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil-in-water cosmetic emulsions such as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, aftersun creams and lotions, hand creams and lotions, depilatory creams and lotions, aftershave creams and lotions, suntan creams and lotions, hair care products such as hairsprays, hair gels, styling lotions, hair conditioners, hair shampoos, permanent and semi-permanent hair dyes, hair shaping compositions such as cold wave agents, wave) and hair smoothing compositions, hair tonics, hair creams and hair lotions and the like, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks and deodorant creams, decorative cosmetics such as eyeliners, eye shadows, nail varnishes, make-up, lipsticks and mascara, and oral and dental hygiene products such as toothpastes, dental floss, mouthwashes, breath fresheners, dental foams, dental gels and dental strips.

[0162] The hygiene products may be selected from incense, insecticides, insect repellents, propellants, rust removers, perfumed freshening wipes, underarm pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, pocket tissues, dishwasher products and deodorants.

[0163] Cleaning compositions, such as cleaners for solid surfaces, may be selected from scented acidic, alkaline and neutral cleaners, such as floor cleaners, window cleaners, hand and machine dishwashing compositions, bathroom and sanitary cleaners, scouring milks, solid and liquid toilet cleaners, powdered and foam carpet cleaners, waxes and polishes, such as furniture polishes, floor waxes, shoe creams, disinfectants, surface disinfectants and sanitary cleaners, brake cleaners, pipe cleaners, limescale removers, grill and oven cleaners, algae and moss removers, mould removers, facade cleaners, etc.

[0164] Fabric detergent compositions may be selected from liquid detergents, powder detergents, laundry pre-treatments such as bleaching agents, soaking agents and stain removers, fabric softeners, laundry soaps, laundry tablets.

[0165] Food means any raw, cooked, or processed edible substance, ice, beverage, or ingredient used or intended for use, in whole or in part, for human consumption, or chewing gum, gummies, jellies, and confectioneries.

[0166] A dietary supplement is a product intended for ingestion that contains edible ingredients intended to add additional nutritional value to food and drink. The edible ingredients can be one or any combination of the following substances: vitamins, minerals, herbs or other botanical substances, amino acids, dietary substances used by people to supplement their diet by increasing their total food intake, concentrates, metabolites, constituents, or extracts. Dietary supplements can be found in many forms, such as tablets, capsules, softgels, gelcaps, liquids, or powders.

[0167] Pharmaceutical compositions include compositions intended for use in the diagnosis, cure, mitigation, treatment or prevention of disease, as well as articles (other than food) intended to affect the structure or any function of the body of humans or other animals.

[0168] Crop protection compositions include compositions intended for the management of plant diseases, weeds, and other pests (both vertebrate and invertebrate) that damage agricultural crops and forests.

[0169] In a preferred embodiment, the composition contains a preservative, an abrasive, an anti-acne agent, an agent for reducing skin aging, an anti-cellulite agent, an anti-dandruff agent, an anti-inflammatory agent, an anti-irritant agent, an irritant soothing agent, an astringent, an antiperspirant, a disinfectant, an anti-static agent, a binder, a buffering agent, a carrier material, a chelating agent, a cell stimulant, a care agent, a depilatory agent, an emulsifier, an enzyme, an essential oil, a fiber, a film former, a fixative, a foam former, a foam stabilizer, an anti-foaming agent, a foam booster, a disinfectant, a gelling agent, a gel forming agent, a hair care agent, a hair shaping agent, a hair smoothing agent, a moisture donating agent, a moisturizing agent, a humectant, a bleaching agent, a strengthening agent, a stain remover, an optical brightener, an impregnating agent, a soil repellent ... repellents, antifriction agents, lubricants, moisturizing creams, ointments, opacifiers, plasticizers, coating agents, polishes, polishes, polymers, powders, proteins, refatting agents, exfoliating agents, silicones, skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, skin whitening agents, skin protectants, emollients, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, UV absorbers, UV filters, fabric softeners, suspending agents, tanning agents, thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids, monounsaturated or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, color-protection agents, pigments, corrosion inhibitors, polyols, electrolytes, and silicone derivatives.

[0170] For example, the method may involve combining a compound of the present invention described herein with: (i) at least one further aroma chemical different from the compound / mixture of the present invention, or (ii) at least one non-fragrance chemical carrier; or (iii) Both (i) and (ii) This can be done by mixing

[0171] The present invention is also directed to a method for modifying the aroma characteristics (e.g., scent characteristics) of an aroma chemical composition, such as a fragranced composition, particularly a fragranced ready-to-use composition, comprising incorporating a compound of the present invention as described herein into the aroma chemical composition, such as a fragranced composition, particularly a fragranced ready-to-use composition.

[0172] In particular, the present invention is directed to a method for preparing a perfume composition, a body care composition, a hygiene article, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising including a compound of the present invention as described herein in the perfume composition, body care composition, hygiene article, cleaning composition, fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0173] In one embodiment, the present invention is directed to a method of imparting notes reminiscent of sweet, fruity, floral, orris, powdery elements to a perfume composition, a body care composition, a hygiene article, a cleaning composition, a fabric detergent composition, a fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition, comprising including a compound of the present invention in the perfume composition, the body care composition, the hygiene article, the cleaning composition, the fabric detergent composition, the fragrance dispenser composition, a food product, a dietary supplement, a pharmaceutical composition or a crop protection composition.

[0174] Embodiment Below, a list of embodiments is provided to further illustrate the present disclosure, but is not intended to limit the disclosure to the specific embodiments listed below.

[0175] 1. Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol to impart a fragrance impression to a composition.

[0176] 2. Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol for imparting a fragrance impression to a composition.

[0177] 3. A method for imparting a fragrance impression to a composition, comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol.

[0178] 4. A method for imparting a fragrance impression to a composition, said method comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol.

[0179] 5. The use or method according to embodiments 1 to 4, wherein the compound is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol.

[0180] 6. The use or method according to any of embodiments 1 to 5, wherein the composition is selected from a perfume composition, a body care composition, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition and a crop protection composition.

[0181] 7. The use or method according to any of embodiments 1 to 6, wherein the impression is selected from the group consisting of aldehyde notes, fatty notes, mandarin notes, clean linen notes, floral notes, marine notes, citrus notes, metallic notes, waxy notes and green notes.

[0182] 8. The use or method according to any of embodiments 1 to 7, wherein the compound is present in an amount in the range of ≧0.01% by weight to ≦70.0% by weight, based on the total weight of the composition.

[0183] 9. a) at least one compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol; and b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol A mixture comprising:

[0184] 10. The mixture according to embodiment 9, wherein the dodeca-4,8-dien-1-ol is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, and mixtures of two or more thereof.

[0185] 11. The mixture according to embodiment 9, wherein the dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

[0186] 12. The mixture according to embodiment 9, wherein the dodeca-4,11-dien-1-ol is selected from (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.

[0187] 13. The mixture according to embodiment 9, wherein 4-dodecen-1-ol is selected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

[0188] 14. The mixture according to embodiment 9, wherein 8-dodecen-1-ol is selected from (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

[0189] 15. The mixture is a) any one or more compounds selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, or b) any one or more compounds selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol, or c) any one or more compounds selected from (a) and (b) 15. A mixture according to any of embodiments 9 to 14, comprising:

[0190] 16. The mixture according to any of embodiments 9-14, wherein the mixture further comprises dodecan-1-ol.

[0191] 17. Use of a mixture according to any one of embodiments 9 to 16 as a fragrance chemical.

[0192] 18. Use of a mixture according to any one of embodiments 9 to 16 for preparing an aroma chemical composition.

[0193] 19. Use of a mixture according to any one of embodiments 9 to 16 for modifying the fragrance characteristics of an aroma chemical composition.

[0194] 20. (i) at least one additional fragrance chemical; (ii) at least one non-fragrance chemical carrier; or (iii) A mixture of (i) and (ii) 17. The aroma chemical composition according to embodiments 1-8 or the mixture according to embodiments 15-16, comprising:

[0195] 21. The aromachemical composition of embodiment 20, which is a fragranced, ready-to-use composition.

[0196] 22. The aromachemical composition of embodiment 21, wherein the perfumed, ready-to-use composition is selected from the group consisting of perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, scent dispenser compositions, foods, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0197] 23. A method for preparing a compound as defined in any one of embodiments 1 to 5, said method comprising: (i) subjecting dodeca-4,8,11-trienal to reduction and hydrogenation, and optionally (ii) isolating said compound. The above method, comprising at least

[0198] Preferred Embodiments 1. a) at least one compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol; and b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol A mixture comprising:

[0199] 2. The mixture according to embodiment 1, wherein the dodeca-4,8-dien-1-ol is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, and mixtures of two or more thereof.

[0200] 3. The mixture according to embodiment 1, wherein the dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

[0201] 4. The mixture according to embodiment 1, wherein the dodeca-4,11-dien-1-ol is selected from (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.

[0202] 5. The mixture according to embodiment 1, wherein 4-dodecen-1-ol is selected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

[0203] 6. The mixture according to embodiment 1, wherein the 8-dodecen-1-ol is selected from (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

[0204] 7. The mixture is a) any one or more compounds selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, or b) any one or more compounds selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol, or c) any one or more compounds selected from (a) and (b) 7. A mixture according to any of embodiments 1 to 6, comprising:

[0205] 8. The mixture according to any of embodiments 1-7, wherein the mixture further comprises dodecan-1-ol.

[0206] 9. Use of a mixture according to any one of embodiments 1 to 8 as a fragrance chemical.

[0207] 10. Use of a mixture according to any one of embodiments 1 to 8 for preparing an aroma chemical composition.

[0208] 11. Use of a mixture according to any one of embodiments 1 to 8 for modifying the fragrance characteristics of an aroma chemical composition.

[0209] 12. A mixture according to any one of embodiments 1 to 8, (i) at least one additional fragrance chemical; (ii) at least one non-fragrance chemical carrier; or (iii) A mixture of (i) and (ii) and a fragrance chemical composition comprising:

[0210] 13. The aromachemical composition of embodiment 12, which is a fragranced, ready-to-use composition.

[0211] 14. The aromachemical composition of embodiment 13, wherein the perfumed, ready-to-use composition is selected from the group consisting of perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, scent dispenser compositions, foods, dietary supplements, pharmaceutical compositions, and crop protection compositions.

[0212] 15. Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol for imparting a fragrance impression to a composition.

[0213] 16. A method for imparting a fragrance impression to a composition, comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol.

[0214] 17. The use or method according to embodiment 15 or 16, wherein the compound is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol.

[0215] 18. The use or method according to any of embodiments 15 to 17, wherein the composition is selected from a perfume composition, a body care composition, a hygiene product, a cleaning composition, a fabric detergent composition, a composition for a scent dispenser, a food product, a dietary supplement, a pharmaceutical composition and a crop protection composition.

[0216] 19. The use or method according to any of embodiments 15 to 17, wherein the impression is selected from the group consisting of aldehyde notes, fatty notes, mandarin notes, clean linen notes, floral notes, marine notes, citrus notes, metallic notes, waxy notes and green notes.

[0217] 20. The use or method according to any of embodiments 15-17, wherein the compound is present in an amount in the range of ≧0.01 wt.% to ≦70.0 wt.%, based on the total weight of the composition. [Example]

[0218] The present invention is further illustrated by the following non-limiting examples. More particularly, the test methods identified hereinafter are part of the general disclosure of this application and are not limited to the specific examples.

[0219] Analysis method: Characterization is 13 This is done by C-NMR. 13 C-NMR spectra were measured on a Bruker DPX-500 spectrometer.

[0220] GC Method: Stabilwax 60m GC column coupled with TOF mass spectrometry FI (field ionization).

[0221] 1. Preparation of 4-dodecadien-1-ol and 8-dodecadien-1-ol as a mixture of cis / trans isomers and a mixture of 4,8-dodecadien-1-ol.

[0222] In a 3.5 L autoclave, 4,8,11-dodecatrienal (1.2 kg, 82 mmol) was dissolved in methanol (800 g) in the presence of trimethylamine (48 g, 3 wt%) and a Ru / Fe catalyst (20 g, 1.6 wt%). The hydrogenation reaction was carried out at T = 55 °C and 30 bar hydrogen pressure to give 4-dodecadien-1-ol and 8-dodecadien-1-ol as a mixture of cis / trans isomers, as well as 4,8-dodecadien-1-ol.

[0223] 1H NMR: Mixture of products: (500 MHz; CDCl3): δ [ppm] = 5,42-5,32 (m), 3,61-3,57 (m), 2,1-1,9 (m), 1,62-1,56 (m), 1,35-1,23 (m).

[0224] Depending on the hydrogenation time, different ratios of the corresponding alcohols were determined by H-NMR (olefin vs methylene).

[0225] [Table A]

[0226] 2. Olfactory assessment A scent strip test was conducted to test the quality and intensity of the odors of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol, and dodecan-1-ol.

[0227] For this purpose, strips of absorbent paper were immersed in a solution containing 1-10% by weight of the compound to be tested in ethanol. After evaporation of the solvent (approximately 30 seconds), the scent impression was evaluated olfactorily by a trained perfumer.

[0228] result:

[0229] [Table 1]

[0230] Advantageous perfume ingredients The compound of Example 1 was formulated into a perfume composition according to Tables 2 and 3 and named Compound A.

[0231] [Table 2]

[0232] [Table 3]

[0233] The fragrance compositions according to Example 1 or Example 2 in Table 1, Table 2, Table 3, i.e. 1A, 1B, 2A, 2B, could be included in various compositions listed below; Deo pump spray Clean Hair Conditioner Face wash gel Foam bath concentrate Hair gel Self-foaming body wash Sprayable sunscreen emulsion Sprayable sun protection emulsion Emollient facial gel Two-phase oil foam bath ·shampoo Shower bath Water-alcohol AP / Deodorant pump spray ·aerosol Water-based / alcohol-based AP / deodorant roll-on "Out of bed" type styling gel Shaving foam · Baby shampoo for sensitive skin Body wash for sensitive skin Shine-boosting shampoo for sensitive scalps Deodorant stick Baby wipes Aftershave balm Face gel ·Face day care cream Face cleanser Body lotion Sun care SPF50+, sprayable lotion Hand dish detergent - Regular Hand dish detergent - concentrate Sanitary cleaning agent - concentrate Multipurpose cleaner Antibacterial fabric softener Detergent compositions Powder detergent composition Liquid detergent compositions

[0234] Those skilled in the art will be familiar with the various common formulation methods for such products.

[0235] Perfume Oil Compositions 1A, 1B, 2A and 2B can be formulated into specific formulations such as those disclosed in IP.com Number: IPCOM000258614D, entitled New Aroma Chemicals, pages 6-46, Tables 1-D13, where "Fragrance Composition 1A" is replaced with an equal amount of Perfume Oil Composition 1A, 1B, 2A or 2B. The present invention includes, for example, the following embodiments. [Section 1] Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol to impart a fragrance impression to a composition. [Section 2] 1. A method for imparting a fragrance impression to a composition, the method comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, 11-dodecen-1-ol and dodecan-1-ol. [Section 3] 3. The use or method according to item 1 or 2, wherein the compound is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol, (8Z)-dodecen-1-ol and dodecan-1-ol. [Section 4] Item 4. The use or method according to any one of items 1 to 3, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, compositions for scent dispensers, foods, dietary supplements, pharmaceutical compositions and crop protection compositions. [Section 5] Item 5. The use or method according to any one of Items 1 to 4, wherein the impression is selected from the group consisting of aldehyde notes, fatty notes, mandarin notes, clean linen notes, floral notes, marine notes, citrus notes, metallic notes, waxy notes, and green notes. [Section 6] Item 6. The use or method according to any one of items 1 to 5, wherein the compound is present in an amount in the range of ≧0.01 wt % to ≦70.0 wt % based on the total weight of the composition. [Section 7] a) at least one compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol; and b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol A mixture comprising: [Section 8] Item 8. The mixture according to item 7, wherein the dodeca-4,8-dien-1-ol is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, and mixtures of two or more thereof. [Section 9] Item 8. The mixture according to item 7, wherein the dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol. [Section 10] Item 8. The mixture according to item 7, wherein the dodeca-4,11-dien-1-ol is selected from (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol. [Section 11] Item 8. The mixture according to item 7, wherein 4-dodecen-1-ol is selected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol. [Section 12] Item 8. The mixture according to item 7, wherein 8-dodecen-1-ol is selected from (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol. [Section 13] The mixture is a) any one or more compounds selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, or b) any one or more compounds selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol, or c) any one or more compounds selected from (a) and (b) Item 13. The mixture according to any one of items 7 to 12, comprising: [Section 14] Item 13. The mixture according to any one of items 7 to 12, wherein the mixture further comprises dodecan-1-ol. [Section 15] 15. Use of a mixture according to any one of paragraphs 7 to 14 as a fragrance chemical. [Section 16] 15. Use of a mixture according to any one of paragraphs 7 to 14 for preparing an aroma chemical composition. [Section 17] 15. Use of a mixture according to any one of paragraphs 7 to 14 to modify the fragrance characteristics of an aroma chemical composition. [Section 18] (i) at least one additional fragrance chemical; (ii) at least one non-fragrance chemical carrier; or (iii) A mixture of (i) and (ii) The aroma chemical composition according to any one of items 1 to 6, or the mixture according to any one of items 16 to 17, comprising: [Section 19] Item 19. The aroma chemical composition of item 18, which is a fragranced, ready-to-use composition. [Section 20] 20. The aroma chemical composition according to clause 19, wherein the perfumed ready-to-use composition is selected from the group consisting of perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, scent dispenser compositions, food products, dietary supplements, pharmaceutical compositions and crop protection compositions. [Section 21] A method for preparing a compound as defined in any one of items 1 to 6, comprising the steps of: (i) subjecting dodeca-4,8,11-trienal to reduction and hydrogenation, and optionally (ii) isolating said compound The above method, comprising at least

Claims

1. 1. Use of a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol to impart a fragrance impression to a composition.

2. A method for imparting a fragrance impression to a composition, the method comprising at least the step of adding to the composition a compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, dodeca-4,11-dien-1-ol, 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol.

3. 3. The use or method of claim 1 or 2, wherein the compound is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, (8E)-dodeca-4,8-dien-1-ol, (8Z)-dodeca-4,8-dien-1-ol, (4E)dodeca-4,11-dien-1-ol, (4Z)dodeca-4,11-dien-1-ol, (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol, and (8Z)-dodecen-1-ol.

4. 4. The use or method according to any one of claims 1 to 3, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, compositions for scent dispensers, foods, dietary supplements, pharmaceutical compositions and crop protection compositions.

5. 5. The use or method according to any one of claims 1 to 4, wherein the impression is selected from the group consisting of aldehyde notes, fatty notes, mandarin notes, clean linen notes, floral notes, marine notes, citrus notes, metallic notes, waxy notes and green notes.

6. 6. The use or method according to any one of claims 1 to 5, wherein the compound is present in an amount ranging from ≥ 0.01% to ≤ 70.0% by weight relative to the total weight of the composition.

7. a) at least one compound selected from the group consisting of dodeca-4,8-dien-1-ol, dodeca-8,11-dien-1-ol, and dodeca-4,11-dien-1-ol; and b) at least one compound selected from the group consisting of 4-dodecen-1-ol, 8-dodecen-1-ol, and 11-dodecen-1-ol Aromatic chemical mixtures including:

8. 8. The aroma chemical mixture of claim 7, wherein the dodeca-4,8-dien-1-ol is selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol, (4Z,8Z)-dodeca-4,8-dien-1-ol, and mixtures of two or more thereof.

9. 8. The aroma chemical mixture of claim 7, wherein the dodeca-8,11-dien-1-ol is selected from (8E)-dodeca-4,8-dien-1-ol and (8Z)-dodeca-4,8-dien-1-ol.

10. 8. The aroma chemical mixture of claim 7, wherein the dodeca-4,11-dien-1-ol is selected from (4E)-dodeca-4,11-dien-1-ol and (4Z)-dodeca-4,11-dien-1-ol.

11. 8. The aroma chemical mixture of claim 7, wherein the 4-dodecen-1-ol is selected from (4E)-dodecen-1-ol and (4Z)-dodecen-1-ol.

12. 8. The aroma chemical mixture of claim 7, wherein the 8-dodecen-1-ol is selected from (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol.

13. The aroma chemical mixture comprising: a) any one or more compounds selected from (4E)-dodecen-1-ol, (4Z)-dodecen-1-ol, (8E)-dodecen-1-ol and (8Z)-dodecen-1-ol, or b) any one or more compounds selected from (4Z,8E)-dodeca-4,8-dien-1-ol, (4E,8Z)-dodeca-4,8-dien-1-ol, (4E,8E)-dodeca-4,8-dien-1-ol and (4Z,8Z)-dodeca-4,8-dien-1-ol, or c) any one or more compounds selected from (a) and (b) 13. The aroma chemical mixture of any one of claims 7 to 12, comprising:

14. The aroma chemical mixture of any one of claims 7 to 12, wherein the aroma chemical mixture further comprises dodecan-1-ol.

15. Use of the aroma chemical mixture according to any one of claims 7 to 14 for preparing an aroma chemical composition.

16. Use of the aroma chemical mixture according to any one of claims 7 to 14 to modify the aroma character of an aroma chemical composition.

17. (i) at least one additional fragrance chemical; (ii) at least one non-fragrance chemical carrier; or (iii) A mixture of (i) and (ii) 17. The aroma chemical composition of any one of claims 1 to 6 or the aroma chemical mixture of any one of claims 15 to 16, comprising:

18. 20. The aroma chemical composition of claim 17, which is a fragranced, ready-to-use composition.

19. 20. The aroma chemical composition of claim 18, wherein the fragranced ready-to-use composition is selected from the group consisting of perfume compositions, body care compositions, hygiene products, cleaning compositions, fabric detergent compositions, scent dispenser compositions, food products, dietary supplements, pharmaceutical compositions and crop protection compositions.

20. A process for preparing a compound as defined in any one of claims 1 to 6, comprising the steps of: (i) subjecting dodeca-4,8,11-trienal to reduction and hydrogenation, and optionally (ii) isolating said compound The above method, comprising at least

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